Here, we argue that contemporary jet substructure techniques might facilitate a more direct measurement of hard medium-induced gluon bremsstrahlung in heavy-ion collisions, and focus specifically on the “soft drop declustering” procedure that singles out the two leading jet substructures. Assuming coherent jet energy loss, we find an enhancement of the distribution of the energy fractions shared by the two substructures at small subjet energy caused by hard medium-induced gluon radiation. Departures from this approximation are discussed, in particular, the effects of colour decoherence and the contamination of the grooming procedure by soft background. Finally, we propose a complementary observable, that is the ratio of the two-pronged probability in Pb-Pb to proton-proton collisions and discuss its sensitivity to various energy loss mechanisms.